Human Metabolome Database Version 3.5

Showing metabocard for DHAP(18:0) (HMDB11133)

Record Information
Version 3.5
Creation Date 2008-10-29 06:24:48 -0600
Update Date 2013-03-26 16:15:27 -0600
HMDB ID HMDB11133
Secondary Accession Numbers None
Metabolite Identification
Common Name DHAP(18:0)
Description DHAP(18:0) is the octadecanoyl derivative of dihydroxyacetone phosphate. It is also known as an alkyl-DHAP. This compound is formed by octadecanoic acid reacting with DHAP. Alkyl-DHAPs are intermediates in the synthesis of ether phospholipids. The initial steps of ether phospholipid biosynthesis take place in peroxisomes. Alkyl-dihydroxyacetonephosphate synthase is the peroxisomal enzyme that actually introduces the ether linkage. Levels of Alkyl-DHAP have been found to be strongly reduced in human fibroblasts derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients. Four other enzymes are known to be involved in the metabolism of acyl-DHAP and alkyl-DHAP. These include: acyl-DHAP/alkyl-DHAP oxidoreductase, DHAP acyltransferase, alkyl-DHAP phosphohydrolase, and a dinitrofluorobenzene-insensitive acyl-DHAP acylhydrolase. Dihydroxyacetone phosphate (DHAP) is a biochemical compound primarily involved in the glycolysis metabolic pathway. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor. DHAP may be referred to as glycerone phosphate in older texts. 1-Octadecyl-glycerone-3-phosphate is an intermediate in Ether lipid metabolism. DHAP(18:0) or 1-Octadecanoyl-glycerone-3-phosphate is the precursor to 1-Octadecyl-glycerone-3-phosphate DHAP(18:0e) which is generated via alkylglycerone phosphate synthase (EC: 2.5.1.26). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked 'bilayers'. (Wikipedia)
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Octadecanoyl DHAP
  2. 1-Octadecanoyl Dihydroxyacetone phosphate
  3. 1-Octadecanoyl-glycerone-3-phosphate
  4. 1-Stearoylglycerone 3-phosphate
Chemical Formula C21H41O7P
Average Molecular Weight 436.5198
Monoisotopic Molecular Weight 436.258990178
IUPAC Name [3-(octadecanoyloxy)-2-oxopropoxy]phosphonic acid
Traditional IUPAC Name 3-(octadecanoyloxy)-2-oxopropoxyphosphonic acid
CAS Registry Number Not Available
SMILES CCCCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=O
InChI Identifier InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h2-19H2,1H3,(H2,24,25,26)
InChI Key GTPATKZCXDKGQS-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class N/A
Other Descriptors
  • 1-acylglycerone 3-phosphate(ChEBI)
  • Aliphatic Acyclic Compounds
Substituents
  • Alpha Ketoaldehyde
  • Carboxylic Acid Ester
  • Ketone
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
Direct Parent Fatty Acid Esters
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 8.470E-04 g/L ALOGPS
LogP 5.37 ALOGPS
LogP 6.16 ChemAxon
LogS -5.71 ALOGPS
pKa (strongest acidic) 1.19 ChemAxon
pKa (strongest basic) -7 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 110.13 A2 ChemAxon
Rotatable Bond Count 22 ChemAxon
Refractivity 113.27 ChemAxon
Polarizability 50.42 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Plasmalogen Synthesis SMP00479 Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027912
KNApSAcK ID Not Available
Chemspider ID 389126 Link_out
KEGG Compound ID C03805 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11133 Link_out
Metagene Link HMDB11133 Link_out
METLIN ID Not Available
PubChem Compound 440127 Link_out
PDB ID Not Available
ChEBI ID 36476 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Alkyldihydroxyacetonephosphate synthase, peroxisomal
Reactions: Not Available
Gene Name: AGPS
Uniprot ID: O00116 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA